# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1845 data_kp56 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 N8 O2' _chemical_formula_weight 424.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y+1/2, z+1/2' '-x, -y, -z' '-x, y-1/2, -z-1/2' _cell_length_a 6.163(1) _cell_length_b 17.243(4) _cell_length_c 18.471(1) _cell_angle_alpha 90.00 _cell_angle_beta 92.00(1) _cell_angle_gamma 90.00 _cell_volume 1961.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.94 _cell_measurement_theta_max 12.62 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9707 _exptl_absorpt_correction_T_max 0.9882 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.710730 _diffrn_radiation_type 'MO k\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method '\w--2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 _diffrn_reflns_number 4175 _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_av_sigmaI/netI 0.0814 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.74 _reflns_number_total 3713 _reflns_number_gt 1842 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express' _computing_cell_refinement 'CAD4 Express' _computing_data_reduction 'XCAD4 (Harms 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0559P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3713 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1173 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1036 _refine_ls_wR_factor_gt 0.0909 _refine_ls_goodness_of_fit_ref 0.842 _refine_ls_restrained_S_all 0.842 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1' O -1.2510(3) 0.86457(13) -0.17602(12) 0.0933(6) Uani 1 1 d . . . O2' O -1.2849(3) 0.93100(15) -0.07896(12) 0.1010(7) Uani 1 1 d . . . N1 N -0.3388(3) 0.77908(10) 0.06698(9) 0.0456(5) Uani 1 1 d . . . N2 N -0.4194(3) 0.75604(10) 0.00245(9) 0.0437(4) Uani 1 1 d . . . N3 N -0.3050(3) 0.70157(10) -0.03178(9) 0.0441(4) Uani 1 1 d . . . N5 N 0.1852(3) 0.63666(10) 0.06680(9) 0.0437(4) Uani 1 1 d . . . N6 N 0.1605(3) 0.68330(10) 0.12557(8) 0.0462(5) Uani 1 1 d . . . N1A N 0.0023(3) 0.77857(11) 0.19344(9) 0.0534(5) Uani 1 1 d . . . N1' N -1.1870(3) 0.88470(14) -0.11560(14) 0.0675(6) Uani 1 1 d . . . N2B N -0.1285(3) 0.90099(13) 0.15725(11) 0.0664(6) Uani 1 1 d . . . C3A C -0.1377(3) 0.68842(11) 0.01500(10) 0.0390(5) Uani 1 1 d . . . C4 C 0.0465(3) 0.63711(12) 0.01198(10) 0.0399(5) Uani 1 1 d . . . C7 C -0.0012(3) 0.73747(13) 0.13535(11) 0.0432(5) Uani 1 1 d . . . C7A C -0.1588(3) 0.73659(12) 0.07484(10) 0.0396(5) Uani 1 1 d . . . C8 C 0.3278(4) 0.67300(15) 0.18275(12) 0.0604(6) Uani 1 1 d . . . H8A H 0.2685 0.6448 0.2223 0.085 Uiso 1 1 calc R . . H8B H 0.3774 0.7228 0.1995 0.085 Uiso 1 1 calc R . . H8C H 0.4475 0.6446 0.1640 0.085 Uiso 1 1 calc R . . C1' C -0.6133(3) 0.78860(12) -0.02807(11) 0.0426(5) Uani 1 1 d . . . C2' C -0.7206(4) 0.84440(13) 0.01063(12) 0.0527(6) Uani 1 1 d . . . H2' H -0.6661 0.8604 0.0558 0.069 Uiso 1 1 calc R . . C3' C -0.9093(4) 0.87612(14) -0.01843(13) 0.0571(6) Uani 1 1 d . . . H3' H -0.9849 0.9134 0.0069 0.074 Uiso 1 1 calc R . . C4' C -0.9837(3) 0.85161(13) -0.08565(12) 0.0494(6) Uani 1 1 d . . . C5' C -0.8791(4) 0.79631(14) -0.12422(12) 0.0510(6) Uani 1 1 d . . . H5' H -0.9342 0.7807 -0.1694 0.066 Uiso 1 1 calc R . . C6' C -0.6917(3) 0.76410(14) -0.09548(11) 0.0492(6) Uani 1 1 d . . . H6' H -0.6182 0.7263 -0.1209 0.064 Uiso 1 1 calc R . . C1" C 0.0892(3) 0.58397(11) -0.04875(10) 0.0404(5) Uani 1 1 d . . . C2" C -0.0634(4) 0.56846(14) -0.10312(11) 0.0530(6) Uani 1 1 d . . . H2" H -0.1974 0.5932 -0.1030 0.069 Uiso 1 1 calc R . . C3" C -0.0201(4) 0.51662(14) -0.15776(12) 0.0596(6) Uani 1 1 d . . . H3" H -0.1254 0.5068 -0.1939 0.078 Uiso 1 1 calc R . . C4" C 0.1756(4) 0.47962(14) -0.15931(12) 0.0551(6) Uani 1 1 d . . . H4" H 0.2034 0.4440 -0.1956 0.072 Uiso 1 1 calc R . . C5" C 0.3307(4) 0.49603(16) -0.10619(13) 0.0642(7) Uani 1 1 d . . . H5" H 0.4651 0.4716 -0.1070 0.083 Uiso 1 1 calc R . . C6" C 0.2895(4) 0.54797(14) -0.05200(12) 0.0553(6) Uani 1 1 d . . . H6" H 0.3974 0.5591 -0.0171 0.072 Uiso 1 1 calc R . . C1B C -0.1543(4) 0.83782(13) 0.19838(11) 0.0495(6) Uani 1 1 d . . . C3B C -0.2868(5) 0.95498(16) 0.15908(14) 0.0720(7) Uani 1 1 d . . . H3B H -0.2741 0.9991 0.1305 0.094 Uiso 1 1 calc R . . C4B C -0.4654(5) 0.94821(16) 0.20086(14) 0.0692(7) Uani 1 1 d . . . H4B H -0.5737 0.9858 0.1994 0.090 Uiso 1 1 calc R . . C5B C -0.4797(4) 0.88492(16) 0.24449(14) 0.0659(7) Uani 1 1 d . . . H5B H -0.5972 0.8796 0.2744 0.086 Uiso 1 1 calc R . . C6B C -0.3218(4) 0.82903(14) 0.24450(12) 0.0520(6) Uani 1 1 d . . . H6B H -0.3281 0.7863 0.2750 0.068 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1' 0.0848(14) 0.1039(16) 0.0883(15) 0.0068(13) -0.0361(12) 0.0155(12) O2' 0.0774(14) 0.1243(18) 0.1008(16) 0.0094(15) -0.0055(12) 0.0474(14) N1 0.0448(11) 0.0532(12) 0.0387(10) -0.0029(9) -0.0004(8) 0.0007(9) N2 0.0421(10) 0.0475(11) 0.0414(10) -0.0037(9) 0.0003(8) 0.0035(9) N3 0.0405(10) 0.0477(11) 0.0439(10) -0.0004(9) -0.0009(8) -0.0007(9) N5 0.0421(10) 0.0483(11) 0.0407(10) -0.0020(9) -0.0001(9) -0.0039(9) N6 0.0440(11) 0.0552(12) 0.0389(10) -0.0081(9) -0.0042(8) 0.0059(9) N1A 0.0521(11) 0.0646(13) 0.0430(11) -0.0110(10) -0.0054(9) 0.0085(10) N1' 0.0523(14) 0.0761(16) 0.0737(16) 0.0257(13) -0.0034(13) 0.0075(12) N2B 0.0757(15) 0.0700(15) 0.0533(12) 0.0005(11) -0.0001(11) 0.0036(13) C3A 0.0378(12) 0.0416(12) 0.0377(11) 0.0036(10) 0.0020(10) -0.0033(10) C4 0.0394(12) 0.0427(12) 0.0375(11) 0.0042(10) 0.0013(10) -0.0049(10) C7 0.0421(12) 0.0464(13) 0.0410(12) -0.0003(10) 0.0016(10) 0.0009(11) C7A 0.0386(12) 0.0420(12) 0.0384(11) 0.0025(10) 0.0036(9) 0.0024(10) C8 0.0574(15) 0.0733(16) 0.0494(13) -0.0107(13) -0.0150(12) 0.0107(13) C1' 0.0368(12) 0.0476(13) 0.0433(12) 0.0069(10) 0.0009(10) 0.0008(11) C2' 0.0483(14) 0.0612(15) 0.0485(13) -0.0041(12) 0.0000(11) 0.0042(12) C3' 0.0534(15) 0.0584(15) 0.0595(15) 0.0047(12) 0.0025(12) 0.0080(13) C4' 0.0418(13) 0.0515(14) 0.0546(14) 0.0187(12) -0.0018(11) 0.0013(12) C5' 0.0501(14) 0.0588(15) 0.0437(12) 0.0110(12) -0.0035(11) -0.0037(12) C6' 0.0489(13) 0.0567(14) 0.0419(12) -0.0014(11) 0.0012(11) 0.0012(12) C1" 0.0441(13) 0.0396(12) 0.0375(11) 0.0030(9) 0.0032(10) -0.0030(10) C2" 0.0518(14) 0.0600(15) 0.0469(13) -0.0056(12) -0.0040(11) 0.0029(12) C3" 0.0696(18) 0.0590(16) 0.0496(14) -0.0100(12) -0.0077(12) 0.0022(14) C4" 0.0665(17) 0.0562(15) 0.0433(13) -0.0089(11) 0.0099(12) -0.0017(13) C5" 0.0573(16) 0.0759(18) 0.0597(15) -0.0114(14) 0.0051(13) 0.0095(14) C6" 0.0480(14) 0.0675(16) 0.0502(14) -0.0130(12) -0.0021(11) 0.0054(13) C1B 0.0564(15) 0.0500(14) 0.0411(12) -0.0093(11) -0.0105(11) 0.0010(12) C3B 0.095(2) 0.0597(17) 0.0608(16) 0.0068(13) 0.0003(15) 0.0109(16) C4B 0.0758(19) 0.0647(17) 0.0668(17) -0.0026(15) -0.0025(15) 0.0225(15) C5B 0.0614(16) 0.0689(17) 0.0678(16) -0.0025(14) 0.0072(13) 0.0080(14) C6B 0.0511(14) 0.0514(14) 0.0538(14) -0.0004(11) 0.0057(12) -0.0016(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1' N1' 1.221(3) . ? O2' N1' 1.220(3) . ? N1 C7A 1.333(2) . ? N1 N2 1.336(2) . ? N2 N3 1.345(2) . ? N2 C1' 1.419(2) . ? N3 C3A 1.341(2) . ? N5 C4 1.302(2) . ? N5 N6 1.364(2) . ? N6 C7 1.382(2) . ? N6 C8 1.461(3) . ? N1A C7 1.285(3) . ? N1A C1B 1.411(3) . ? N1' C4' 1.468(3) . ? N2B C1B 1.341(3) . ? N2B C3B 1.350(3) . ? C3A C7A 1.392(3) . ? C3A C4 1.442(3) . ? C4 C1" 1.479(3) . ? C7 C7A 1.455(3) . ? C1' C2' 1.381(3) . ? C1' C6' 1.386(3) . ? C2' C3' 1.377(3) . ? C3' C4' 1.375(3) . ? C4' C5' 1.366(3) . ? C5' C6' 1.371(3) . ? C1" C2" 1.378(3) . ? C1" C6" 1.385(3) . ? C2" C3" 1.381(3) . ? C3" C4" 1.366(3) . ? C4" C5" 1.375(3) . ? C5" C6" 1.373(3) . ? C1B C6B 1.369(3) . ? C3B C4B 1.371(3) . ? C4B C5B 1.361(3) . ? C5B C6B 1.370(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7A N1 N2 102.48(16) . . ? N1 N2 N3 116.23(15) . . ? N1 N2 C1' 121.26(17) . . ? N3 N2 C1' 122.50(16) . . ? C3A N3 N2 102.65(16) . . ? C4 N5 N6 121.78(17) . . ? N5 N6 C7 127.15(16) . . ? N5 N6 C8 114.07(17) . . ? C7 N6 C8 118.78(17) . . ? C7 N1A C1B 117.51(18) . . ? O2' N1' O1' 122.9(2) . . ? O2' N1' C4' 118.5(2) . . ? O1' N1' C4' 118.6(2) . . ? C1B N2B C3B 116.5(2) . . ? N3 C3A C7A 108.64(17) . . ? N3 C3A C4 131.86(18) . . ? C7A C3A C4 119.49(18) . . ? N5 C4 C3A 118.03(18) . . ? N5 C4 C1" 117.18(18) . . ? C3A C4 C1" 124.79(17) . . ? N1A C7 N6 119.40(18) . . ? N1A C7 C7A 129.65(19) . . ? N6 C7 C7A 110.94(18) . . ? N1 C7A C3A 109.98(17) . . ? N1 C7A C7 127.49(18) . . ? C3A C7A C7 122.53(18) . . ? C2' C1' C6' 121.3(2) . . ? C2' C1' N2 118.81(18) . . ? C6' C1' N2 119.92(19) . . ? C3' C2' C1' 119.2(2) . . ? C4' C3' C2' 118.7(2) . . ? C5' C4' C3' 122.5(2) . . ? C5' C4' N1' 119.2(2) . . ? C3' C4' N1' 118.3(2) . . ? C4' C5' C6' 119.2(2) . . ? C5' C6' C1' 119.1(2) . . ? C2" C1" C6" 117.9(2) . . ? C2" C1" C4 122.56(19) . . ? C6" C1" C4 119.53(19) . . ? C1" C2" C3" 120.9(2) . . ? C4" C3" C2" 120.7(2) . . ? C3" C4" C5" 118.8(2) . . ? C6" C5" C4" 120.9(2) . . ? C5" C6" C1" 120.8(2) . . ? N2B C1B C6B 123.3(2) . . ? N2B C1B N1A 117.2(2) . . ? C6B C1B N1A 119.5(2) . . ? N2B C3B C4B 123.4(2) . . ? C5B C4B C3B 118.1(2) . . ? C4B C5B C6B 120.2(2) . . ? C1B C6B C5B 118.2(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7A N1 N2 N3 0.2(2) . . . . ? C7A N1 N2 C1' -178.83(17) . . . . ? N1 N2 N3 C3A 0.3(2) . . . . ? C1' N2 N3 C3A 179.38(17) . . . . ? C4 N5 N6 C7 -2.3(3) . . . . ? C4 N5 N6 C8 178.05(19) . . . . ? N2 N3 C3A C7A -0.7(2) . . . . ? N2 N3 C3A C4 -179.6(2) . . . . ? N6 N5 C4 C3A -0.4(3) . . . . ? N6 N5 C4 C1" -179.83(17) . . . . ? N3 C3A C4 N5 -179.8(2) . . . . ? C7A C3A C4 N5 1.5(3) . . . . ? N3 C3A C4 C1" -0.4(3) . . . . ? C7A C3A C4 C1" -179.17(18) . . . . ? C1B N1A C7 N6 174.50(19) . . . . ? C1B N1A C7 C7A -7.3(3) . . . . ? N5 N6 C7 N1A -178.00(19) . . . . ? C8 N6 C7 N1A 1.6(3) . . . . ? N5 N6 C7 C7A 3.5(3) . . . . ? C8 N6 C7 C7A -176.93(18) . . . . ? N2 N1 C7A C3A -0.7(2) . . . . ? N2 N1 C7A C7 179.33(19) . . . . ? N3 C3A C7A N1 1.0(2) . . . . ? C4 C3A C7A N1 179.97(17) . . . . ? N3 C3A C7A C7 -179.07(18) . . . . ? C4 C3A C7A C7 -0.1(3) . . . . ? N1A C7 C7A N1 -0.5(4) . . . . ? N6 C7 C7A N1 177.78(19) . . . . ? N1A C7 C7A C3A 179.5(2) . . . . ? N6 C7 C7A C3A -2.2(3) . . . . ? N1 N2 C1' C2' -0.8(3) . . . . ? N3 N2 C1' C2' -179.86(18) . . . . ? N1 N2 C1' C6' 179.30(18) . . . . ? N3 N2 C1' C6' 0.3(3) . . . . ? C6' C1' C2' C3' 0.1(3) . . . . ? N2 C1' C2' C3' -179.77(19) . . . . ? C1' C2' C3' C4' -0.6(3) . . . . ? C2' C3' C4' C5' 0.9(3) . . . . ? C2' C3' C4' N1' 178.9(2) . . . . ? O2' N1' C4' C5' 176.2(2) . . . . ? O1' N1' C4' C5' -3.7(3) . . . . ? O2' N1' C4' C3' -1.9(3) . . . . ? O1' N1' C4' C3' 178.2(2) . . . . ? C3' C4' C5' C6' -0.5(3) . . . . ? N1' C4' C5' C6' -178.5(2) . . . . ? C4' C5' C6' C1' -0.1(3) . . . . ? C2' C1' C6' C5' 0.3(3) . . . . ? N2 C1' C6' C5' -179.87(19) . . . . ? N5 C4 C1" C2" 167.7(2) . . . . ? C3A C4 C1" C2" -11.6(3) . . . . ? N5 C4 C1" C6" -12.4(3) . . . . ? C3A C4 C1" C6" 168.3(2) . . . . ? C6" C1" C2" C3" 2.1(3) . . . . ? C4 C1" C2" C3" -178.0(2) . . . . ? C1" C2" C3" C4" -0.2(3) . . . . ? C2" C3" C4" C5" -1.2(4) . . . . ? C3" C4" C5" C6" 0.7(4) . . . . ? C4" C5" C6" C1" 1.3(4) . . . . ? C2" C1" C6" C5" -2.7(3) . . . . ? C4 C1" C6" C5" 177.4(2) . . . . ? C3B N2B C1B C6B -4.7(3) . . . . ? C3B N2B C1B N1A 175.9(2) . . . . ? C7 N1A C1B N2B -72.5(3) . . . . ? C7 N1A C1B C6B 108.1(2) . . . . ? C1B N2B C3B C4B 0.9(4) . . . . ? N2B C3B C4B C5B 2.2(4) . . . . ? C3B C4B C5B C6B -1.8(4) . . . . ? N2B C1B C6B C5B 5.2(3) . . . . ? N1A C1B C6B C5B -175.5(2) . . . . ? C4B C5B C6B C1B -1.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.74 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.158 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.037